N+P Travel Guide: Tri-State NY-CT-MA

New York, Connecticut, Massachusetts. Whether you live in New York City or not, you may be surprised to learn that visiting three states in one day is not only possible, it's actually easy to do and relaxing to boot (especially if you don't mind road trips).

I love to turn up the radio while taking in the natural beauty of the tri-state area. Going for a joy ride is actually a joy because I don't own a car, and driving is a welcome change of pace from buses, subways, taxis, and walking. Choose your own adventure by visiting a handful of the places I have mentioned below; get lost on purpose, then use the map I created to find your way back; grab a friend or take a day for yourself!

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Start Here
Take the Metro North train from Grand Central or Harlem-East 125th Street to North White Plains. Walk across the street to Hertz and get in your rental car.

If you take Route 22 to Route 44 all the way up to Salisbury, CT (which I recommend - the drive is pretty scenic), drop by a few of these places.

  • Red Rooster Drive-In
    Good for a hot dog, a milkshake and a quick stretch of the legs.
    1566 NY-22, Brewster, NY 10509

  • Appalachian Trail at Pawling, NY
    Spend most of your day hiking out to the Dover Oak tree - a 300 year old behemoth that is more than 20 feet wide and said to be largest oak tree on the AT - and Nuclear Lake. Or, take a short walk down the boardwalk to get a closer look at the surrounding freshwater wetlands then head back to the car.
    991 Route 22, Pawling, NY 12564

  • Big W's Roadside Bar-B-Que
    If you're really hungry and can't wait to reach, say, Salisbury or Great Barrington, stop here and order some brisket. Bon Appetit and The New York Times have sung Big W's praises and I am joining the chorus.
    1475 NY-22, Wingdale, NY 12594

  • Wassaic Project
    Bridging the gap between rural communities and contemporary art, the Wassaic Project in Wassaic, NY hosts many artists, exhibitions, and events throughout the year, with the goal to revitalize the hamlet while preserving its history (which dates back to the mid-1800s).
    37 Furnace Bank Road, Wassaic, NY 12592

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Millerton, NY
You have reached your last stop in New York before heading on to Connecticut and Massachusetts. 

  • Harney & Sons Tea
    What began as craft tea blended by John Harney, proprietor of the White Hart Inn in Salisbury, CT in the early 1980s, has become a global tea operation headquartered in Millerton, NY. With over two hundred and fifty teas to choose from, visit their tasting room and lounge or, if you've timed your day trip right, stop by their nearby factory for a tour.
    13 Main Street, Millerton, NY 12546

  • Irving Farm Coffee House
    Yes, the very same you frequent at many different locations in NYC!
    44 Main Street, Millerton, NY 12546

  • Oakhurst Diner
    Kimchi at a diner? Yes. They also have amazing milkshakes and organic, grass-fed beef burgers all served inside a classic 1940s box car.
    19 Main Street, Millerton, NY 12546

  • The Millerton Farmers Market
    This farmers market has everything from fresh flowers to produce, cheese and charcuterie to baked goods, and even amazing vegan Indian food. Weren't you planning on having a picnic later?
    6 Dutchess Avenue, Millerton, NY 12546

  • Harlem Valley Rail Trail
    What once saw train traffic since the later half of the 1800s, became a deserted rail line in 1980. Transformed into a paved corridor for pedestrians and cyclists alike, the first section of the HVRT opened in 1996. Subsequent sections have opened since then and have extended the trail from Wassaic, NY to Hillsdale, NY - with plans to open future sections as north as Chatham, NY.
    Southwest of 18 Main Street, Millerton, NY 12546

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Follow Route 44 through Millerton, NY until you reach... 

  • Route 112
    Take this road towards the Hotchkiss School/Sharon, CT for some really spectacular views.

  • Deano's Pizzeria
    Can't wait to eat lunch and in the mood for a slice? Deano's is pretty decent and somehow made better when eaten at a picnic table by Lake Wononscopomuc.
    24 Millerton Road #1, Lakeville, CT 06039

  • On The Run Coffee Shop
    If you don't plan on stopping in Salisbury, grab a coffee, bacon-egg-and-cheese on a roll, and local paper at On The Run before getting back on the road.
    4 Ethan Allen Street, Lakeville, CT 06039

  • Salmon Kill Road
    Make a right on Salmon Kill Road for my favorite stretch of road between Salisbury, CT and Limerock, CT. Also, how convenient, you'll find yourself back on Route 112. You could also follow 112 to Salmon Kill to Salisbury (see above).

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Salisbury, CT
You've arrived at a magical little town. (I lived in Salisbury for a couple of summers, so I might be a bit biased.)

  • Scoville Memorial Library
    Fresh off of your Salmon Kill Road detour, stop by the first free public library in the United States which was established in 1771 and at its current location since the early 1890s. If it's Saturday, be on the lookout for a small, but worthwhile, farmers market out front.
    38 Main Street, Salisbury, CT 06068

  • Mountain Falls Farm
    The Mountain Falls Farm stand at the Salisbury Farmers Market is something special. Run by a geologist-come-farmer, Skip Hobbs, and his wife, their beef is grass-fed and organically raised (as is their produce). The main event is their salad mix "with a zing!" which Hobbs creates on site to the customer's taste. Among the options are kale, arugula, mustard greens, lemon basil, mint, and edible flowers. The farm, located in nearby Sheffield, MA, has been in the family since the mid-1900s.

  • Sweet William's Bakery
    Run, don't walk, to one of my favorite bakeries, but look both ways if you have to cross the busy main street! Among their offerings: ice cream sandwiches featuring Jane's Ice Cream (Kingston, NY), so many baked goods, and coffee from Barrington Coffee Roasting Company (Boston, MA) - aren't you glad you held off on getting coffee at On The Run? (I usually stick to my favorites: a dirty turmeric ginger latte, cinnamon buns, apricot ginger scones, and ginger molasses cookies.)
    17 Main Street, Salisbury, CT 06068

  • LaBonne's Market
    If you don't have time to head up to the Berkshire Mountain Bakery's headquarters in MA, stop in at LaBonne's to pick up some loaves of their bread (literally, the best) and be on the lookout for Appalachian Trail hikers too! Maybe split a deli counter wrap with one of them, and don’t forget to ask them their trail name.
    22 Academy Street, Salisbury, CT 06068

  • White Hart Inn
    Take note of the Civil War Memorial in front of the White Hart Inn or stop in the newly opened Provisions before you leave Salisbury. A small cafe with modern general store vibes, Provisions offers local coffee from Six Depot, breakfast, lunch, and a curated selection of dry goods. The Inn has seen many iterations since it first opened in the 1800s and its restaurant, Tap Room, (serving locally sourced, seasonal food) has been touted as its best amenity by The New York Times.
    15 Under Mountain Road, Salisbury, CT 06068

  • Lion's Head Trail
    There is a beautiful lookout point at the end of the Lion's Head Trail - probably one of the best in the area. Plus, you can work off all those cinnamon buns you just ate.
    84 Bunker Hill Road, Salisbury, CT 06068

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Route 41
Once you’ve passed the state border, slow down and look to your right out over a rolling field that may or may not be occupied by Highland cows and hay bales. This picturesque field is a favorite. 

Continue all the way on Route 41 into downtown Great Barrington, or make a right on Berkshire School Road to pass through sleepy Sheffield, following Route 7 north into Great Barrington.

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Great Barrington, MA
You've made it. Three states in one day. Ostensibly end your journey here, or continue on after checking out a few (or all) of my favorites below.

  • Guido's Fresh Marketplace
    Who doesn't love a thoughtful, well-stocked market? (You can get Berkshire Mountain Bakery bread here too.)
    760 South Main Street, Great Barrington, MA 01230

  • Berkshire Co-Op Market
    Cooperatively owned and community focused!
    42 Bridge Street, Great Barrington, MA 01230

  • Baba Louie's Pizza
    Some of the best pizza you will have in your life. Organic, sourdough, and wood-fired. My favorites include the Dolce Vita, the Ricardo's Pizza Famosa, and the Isabella Pizzarella.
    286 Main Street, Great Barrington, MA 01230

  • Rubi's Cafe
    A quaint coffee shop and cafe tucked away behind the buildings on Main Street, which showcases products from Rubiner's, its sister property.
    264 Main Street, Great Barrington, MA 01230

  • Rubiner's Cheesemongers & Grocers
    Owned by a former military policy analyst and accomplished cheesemonger, Matthew Rubiner's love of cheese, and its history, shows at Rubiner's. No wonder it is a Berkshires favorite.
    264 Main Street, Great Barrington, MA 01230

  • SoCo Creamery
    All natural and sourced from New England family farms, SoCo has been serving up delicious ice cream since 1989.
    5 Railroad Street, Great Barrington, MA 01230

  • One Mercantile
    Opened in 2013, One Mercantile offers small production, vintage production, and fair trade home goods and gifts.
    8 Castle Street, Great Barrington, MA 01230

  • Twigs GB
    A well-appointed clothing, shoe, and accessory boutique off of Main Street. I always buy a pair wool crew socks when I come here. I can't help myself.
    24 Railroad Street, Great Barrington, MA 01230

  • Barrington Outfitters
    A family-owned business that's been selling clothing, footwear, and furniture out of the Main Street storefront since 1994. (I’ve found some amazing shoes here.)
    289 Main Street, Great Barrington, MA 01230

  • Berkshire Mountain Bakery
    When you get out of the car, take a deep breath. You can smell the gluten and it is good. Baker Richard Bourden has been making European-style bread out of the Housatonic, MA location since 1986 and is a pioneer in the fermentation movement. You will not be disappointed for making the extra effort to visit this bakery.
    367 Park Street, Housatonic, MA 01236

UPDATE: September 3, 2018
One Mercantile - Great Barrington, MA